The Question From David Letterman That Made Jennifer Aniston Uncomfortable

In 2006, Jennifer Aniston appeared on David Letterman's talk show, in which she had come to promote "The Break-Up," a 2006 romantic comedy film in which she starred alongside Vince Vaughn (who also co-wrote and produced the film). The interview started on an awkward note, when Letterman complimented Aniston on her legs (comments which he went on to repeat numerous times throughout the interview), then began to press her on whether she was dating Vaughn. Aniston was in fact dating Vaughn at the time; they got together in 2005 while shooting the film, per People, but would break up later in 2006, though she was clearly reticent to talk about it. 

After discussing her legs, Letterman kicked off the interview by asking Aniston if it was Vaughn's idea to have her "appear naked in the movie." Aniston, at first flustered, responded by telling him he should have asked Vaughn that when he was on the show. 

When Letterman went on to say that Vaughn got "all squirrelly" when he asked him about whether he was dating Aniston, she responded by immediately turning the conversation around, asking Letterman about his feud with Oprah Winfrey. After following her on this tangent, Letterman immediately went back to Vaughn, in an exchange which went on for several minutes until Aniston finally pleaded, "Let's move on." In the end, Aniston never answered the question, but very clearly demonstrated how uncomfortable she was with it. 

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